Ligand‐Controlled Tunable Distal C( sp 2 )–H Functionalization of Aryl and Benzyl Phosphonates
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| Natura: | Artículo Open Access |
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Wiley
2026
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| author | Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang |
| author_facet | Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang |
| collection | Wiley Open Access |
| contents | Ligand‐Controlled Tunable Distal C( sp 2 )–H Functionalization of Aryl and Benzyl Phosphonates Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang Transformative Chemistry ABSTRACT Achieving regioselective C–H functionalization is a particularly difficult issue in organic chemistry when these C–H bonds have similar reactivity. Although significant progress has been made in regioselective C–H functionalization at one specific site, the tunable version of such processes is rarely documented. Here we describe a tunable meta ‐ and para ‐selective C–H borylation of aryl and benzyl phosphonates, in which the regioselectivity can be switched by bifunctional ligands. A broad range of substrates are compatible and exhibit good to excellent regioselectivity under mild reaction conditions. Benzyl phosphonates can be conveniently transformed into styrene derivatives via Horner–Wadsworth–Emmons olefination. Gram‐scale preparation and derivatization of borylated products demonstrate the important application of our method in synthetic chemistry. The orthogonality of two functional Bpin and phosphorylmethyl groups provides ample opportunity for increasing the diversity of styrene derivatives with precise site‐control. 10.1002/tch2.70010 http://creativecommons.org/licenses/by/4.0/ |
| doi_str_mv | 10.1002/tch2.70010 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_tch2_70010 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| publishDate | 2026 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Ligand‐Controlled Tunable Distal C( sp 2 )–H Functionalization of Aryl and Benzyl Phosphonates Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang Transformative Chemistry Ligand‐Controlled Tunable Distal C( sp 2 )–H Functionalization of Aryl and Benzyl Phosphonates Han Ang Yajun Wang Jiawei Ma Shengmeng Qin Shuo Lu Wenju Chang Yong Liang Transformative Chemistry ABSTRACT Achieving regioselective C–H functionalization is a particularly difficult issue in organic chemistry when these C–H bonds have similar reactivity. Although significant progress has been made in regioselective C–H functionalization at one specific site, the tunable version of such processes is rarely documented. Here we describe a tunable meta ‐ and para ‐selective C–H borylation of aryl and benzyl phosphonates, in which the regioselectivity can be switched by bifunctional ligands. A broad range of substrates are compatible and exhibit good to excellent regioselectivity under mild reaction conditions. Benzyl phosphonates can be conveniently transformed into styrene derivatives via Horner–Wadsworth–Emmons olefination. Gram‐scale preparation and derivatization of borylated products demonstrate the important application of our method in synthetic chemistry. The orthogonality of two functional Bpin and phosphorylmethyl groups provides ample opportunity for increasing the diversity of styrene derivatives with precise site‐control. 10.1002/tch2.70010 http://creativecommons.org/licenses/by/4.0/ |
| title | Ligand‐Controlled Tunable Distal C( sp 2 )–H Functionalization of Aryl and Benzyl Phosphonates |
| topic | Transformative Chemistry |
| url | https://onlinelibrary.wiley.com/doi/10.1002/tch2.70010 |